Optionality: How to Survive and Thrive in a Volatile World

Generating better options is much more important than being a perfect decision-maker.

In trying to overcome problems of akrasia, we hear a lot about 'willpower' and 'grit'. I say these are dirty words, suitable only for masochists. Trying to do anything through sheer strength of will is like rowing into a headwind: exhausting, and largely futile. The purpose of this book is to set up systems that keep the wind at our backs, marshal

The ends of the barbell don’t have to be equally weighted. In Antifragile, Nassim Taleb describes a barbell tilted 85 to 90 per cent to ultra-conservative assets, like cash or T-bills, and the remaining 10 to 15 per cent spread between small, speculative bets (Fig. 4.2).

“If you think extraordinary talent and a maniacal pursuit of excellence are necessary for success, I say that’s just one approach, and probably the hardest. When it comes to skills, quantity often beats quality.” Adams calls this strategy the ‘talent stack’. The idea is that you combine two or more skills you’re pretty good at, until no-one else ha

The mundane reality is that winning is mostly about not-losing. Think of a counterintelligence agency which works tirelessly behind the scenes to foil terrorist plots: if it’s doing its job well, we’ll never notice anything at all. Most risk accumulates silently in the background, and is attenuated just as silently. ‘Winning’ is making it to 40 wit

The asymmetry of reading only remains juicy if we treat books like the cheap options they are. That means bailing out at the earliest possible opportunity, skimming with abandon, being promiscuous in our appetites, and abandoning the idea that it's virtuous to slog through some interminable volume for the sake of completion.

On the ‘safe’ side, I have some cash for liquidity and emergencies, with the rest of my portfolio invested in the cheapest, broadly diversified index funds I can buy. I don’t try to pick hot stocks, and will never make more (or less) than the average market return. I’ll be holding this portfolio through thick and thin for the next several decades,

Until recently, the conventional wisdom was that there was no extra benefit after a certain point—$70,000 being the magic number most often bandied about. Now we have a ton more research, spanning hundreds of thousands of people across more than 140 countries, this turns out to be wrong. In fact, if you chart a graph of income and happiness, you fi

Here's the one piece of advice Peter Thiel wishes he could give his younger self: there is no need to wait. If you have a 10-year plan, think carefully about whether you can achieve it in the next six months. Sometimes, this exercise will reveal that you really do have to take the long way. Other times, it will reveal that you’re telling yourself a